Azo dyestuffs



Patented Mar. 29,1932

a I RICHARD sTiTssER, or COLOGNE-DEUTZ, ennivrenxessreivon "i'o GENERAL Amman WORKS,,.IN'C.,OF NEW'YORK, N, Y., n con'roimrionjon' DELAWARE Azo nyiisrurrs N Drawing; Application fi led li'ebruary 16, 1928, Serial No.254,902, and in Germany February 28, 1927.

The present invention relates to n'ew disazodyestuffs, more particularly to dyestufis of the generalformula: I

wherein R stands for a sulfonated benzene nucleus. I 7v These dyestuffs are obtainable by coupling one molecule of tetrazotized sulfonic acids 7 of 4.4L-diamino-diphenyl-ureas of the gen-' eral formula soul NH NH2 (0 V I \NH NHz,

" SOaH :wherein the hydrogen atoms of the benzene nuclei may be replaced by alkoxy or halogen,

with two molecules of a sulfonic acid of an 1" aceto-acetic acid arylide of the general formula OHa' .1 H2 V 0.NH.R

wherein R stands for a sulfonated benzene nucleus, which may be otherwise substituted by alkoxy or halogen. In spite of the many 4o sulfo groups present in the molecule, the dye pounds, or by sulfonating the azo dyestuifs from para nitraniline'or para nitraniline sulfonic acids with unsulfonated aceto-acetic acid arylides before or after the reduction H of the nitro group and converting the same into urea compounds, or also by sulfonating' the dyestufi'sfrom 4:4"-diamino -diphenyl V r urea or derivatives thereof with unsulfonated acetoacetic acid arylides. V

The new dyestuffs after being dried and pulverized form yellow to orange powders.

easily soluble in water, sparingly in the usual organic solvents, soluble. in strong sulfuric acid with ayellow coloration. They dye cotton and artificial sill: bright yellow shades fast to Water and washing with soap and soda solution and may also be'usedas lakecolors v and for dyeing paper. y 1 05 The following examples ar'eintendedjto illustrate my invention, Without limitingit thereto V Ewample 1. 4 02 parts by weight of 4:4- diamino-diphenyl-urea-3 3' disulfonic acid '70 aretetrazotizedand coupled with 574 parts by weight of acetoaceticacid ortho 'anisidi'd sulfonic acid in a solutionrenderedalkaline by sodium carbonate. The dyestufi" having 7 in the free state the following formula: e

. CH8 I (5 OCH; o ,7 i so N=N('JHO o- N H \NH N=NCHOONH i I SOaH CH3 is then salted out, filtered and dried, an'orange powder being obtained, which dissolves in water with a yellow coloration, Cotton is dyeda clear deep yellow, whichisfaSt to water, On viscose silk the dyestuif gives a golden yellow, fast to water and to Washing.

7 The new dyestufi' can also be precipitatedon alumina, following the known methods therefor; whereby a deep yellow likewise ob- V e l tained.- v

Y Example 2.402 parts by weight of 4: 4'- diamino-diphenyl-urea-3.3disulfonic acid are tetrazotized and coupled with 58l'-parts of acetoacetic acid-ortho-chloi'anilide in a 7 solution rendered alkaline by sodium carbonate". The dyestufl-is then salted ouafilteree 4000 parts by weight of a sulfuric acid monohydrate. Then 400 parts by weight of oleum mixture is stirred at to ture is then poured washed with water. solved in sodium carbonate and the nitro group reduced to the amino group in the known manner by means of sodium sulfide, after which the urea compound is produced from the amino azo dyestufi" by passing phosgene into the aqueous solution of the dyestutt. The finished dyestufi is then filtered and dried and forms a yellow powder, which dyes cotton and artificial silk yellow shades, possessing satisfactory fastness properties. 2 EwampZe,., L.2 l8 parts by weight of 5-111- tIO-Q itIliSldlIlG-QeStllfOIllC acid are diazotized in the customary manner in water with 69 parts by weight of sodium nitrite and 400 parts by weight of hydrochloric acid of 19 30 B. and coupled with 287 parts by weight of aceto acetic acid-ortho-anisidid sulfonic acid, rendered alkaline by means of sodium carbonate. The dyestuff is salted out, filtered, then dissolved in water andreduced to the amino azo dyestutf with the calculated quantity of sodium sulfide in the presence of caustic soda. The amino-azo dyestuff I is salted out, filtered and treated in aqueous solution with phosgene until the formation of the urea compound is complete. The resulting new dyestuft is then filtered and dried. It forms a reddish yellow powder, which dyes cotton and artificial silk yellow on to ice, filtered and L15 shades, possessing satisfactory fastness properties.

I claim e 1. As a new product the disazo dyestuff having in its free form the probable formula so H v on;

- l 3 to 0on3 /NH, N=N- n 5031,

. ONH CHa NH N=NtH SOH to-NH- V 03H v (SCH:

said dyestufi' being in form of its alkali metal salts a yellow powder, dissolving in water and strong sulfuric acid with a yellow coloraea tion, dyeing cotton clear yellow, viscose silk 0t anhydride content are added and the V V C. until sulfonation is complete. The sultonation mix The dyestutt is then ,dis-

golden-yellow shades, fast to water and washing with soap and soda solution.

2. A new products disazo dyestuffs having in their free form probably the general tormula:

SiOaH wherein R stands for a sulfonated benzene nucleus and wherein the nuclei may be further substituted by alkoXy or halogen, said products being in form of their. alkali metal salts yellow to orange powders, easily soluble in water, sparingly soluble in the usual organic solvents, soluble in strong sulfuric acid with a yellow coloration, dyeing cotton and artificial silk yellow shades of good tastness to water and washing with soapand soda solution.

In testimony whereof I have hereunto setmy hand.

RICHARD STUSSER. 

